Videos from iTMS will not sync

Movies and TV shows that I have purchased from the iTunes Store will not sync to my TV. I have a few a video I have made myself in iTunes and those copied perfectly fine, but the videos from the iTunes Store will not transfer.
I have tried restarting iTunes, my computer, and the TV.
These video files stream perfectly fine, but will not sync.
Any ideas?
Thanks!

Yep...I have followed all of those steps.
I am able to get everything else to sync correctly, just not videos from the iTunes Store.
For example: I select the shows I want to sync. Then I click "Apply" and then I click "Sync". The sync bar spins in the iTunes display and then the Apple logo appears after a few seconds. I do not receive any sort of error message.
Thanks

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